Nitric Acid → HCID 19027049, compound

HRID 1032941Notes

Reaction equation

HRID 1032941 reaction equation
[N+:1]([O-:4])(O)=[O:2].[C:5]([C:8]1[CH:9]=[CH:10][C:11]([O:18][CH3:19])=[C:12]2[C:17]=1[CH2:16][CH2:15][CH2:14][CH2:13]2)(=[O:7])[CH3:6].S(=O)(=O)(O)O>C(OC(=O)C)(=O)C>[C:5]([C:8]1[CH:9]=[C:10]([N+:1]([O-:4])=[O:2])[C:11]([O:18][CH3:19])=[C:12]2[C:17]=1[CH2:16][CH2:15][CH2:14][CH2:13]2)(=[O:7])[CH3:6]

Participants

6

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 19027071HCID 19027071, compound

Product 1

HCID 19027049HCID 19027049, compoundYield 59.4%

Reagents, catalysts & solvents 2

HCID 7918Acetic AnhydrideCatalystHCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 100% nitric acid (0.42 ml, 10 mmol) in 2 ml of acetic anhydride was added dropwise with stirring at <10° to <15° C. to a solution of 8-acetyl-1,2,3,4-tetrahydro5-methoxynaphthalene (2.1 g, 10 mmol) in 25 ml of acetic anhydride containing one drop of conc. sulfuric acid. Stirring was continued for 20 min. at the same temperature, then the reaction mixture was poured into 100 ml of icewater. The precipitated crystals were collected by filtration and washed with water and a small amount of cold ethanol to give 1.48 g (59%) of the title compound. M.p. 76°-77° C.; 1H-NMR (CDCl3) 1.60-1.93 (m, 4H, 2CH2), 2.57 (s, 3H, COCH3), 2.67-3.13 (m, 4H, 2CH2), 3.88 (s, 3H, OCH3), 7.97 (s, 1H, H-7).

Workup

  1. additionthe reaction mixture was poured into 100 ml of icewater
  2. filtrationThe precipitated crystals were collected by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-92b4297a6cdd454c9d9f9e3432b58d35
Source dataset
uspto-grants-1994_05
Patent number
US05308845

Reaction notes

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